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Featuring new experiments, a new essay, and new coverage of nanotechnology, this organic chemistry laboratory book offers a comprehensive treatment of laboratory techniques including small-scale and some microscale methods that use standard-scale ("macroscale") glassware and equipment. The book is organized based on essays and topics of current interest and covers a large number of traditional organic reactions and syntheses, as well as experiments with a biological or health science focus. Seven introductory technique-based experiments, thirteen project-based experiments, and sections on green chemistry and biofuels, spark reader interest.

Introduction

Welcome to Organic Chemistry

Laboratory Safety

Organization of the Textbook

Advance Preparation

Budgeting Time

Purpose

Introduction to Basic Laboratory Techniques

Solubility

Crystallization

Extraction

A Separation and Purification Scheme

Extractions with a Separatory Funnel

Extractions with a Screw-Cap Centrifuge Tube

Chromatography

Thin-Layer Chromatography

Selecting the Correct Solvent for Thin-Layer Chromatography

Monitoring a Reaction with Thin Layer Chromatography

Column Chromatography

Simple and Fractional Distillation

Infrared Spectroscopy and Boiling-Point Determination Essay

Aspirin

Acetylsalicylic Acid

Essay

Analgesics

Acetaminophen

Essay

Identification of Drugs

TLC Analysis of Analgesic Drugs

Essay

Caffeine

Isolation of Caffeine

Extraction of Caffeine from Tea

Isolation of Caffeine from a Tea Bag

Essay

Esters--Flavors and Fragrances

Isopentyl Acetate (Banana Oil)

Essay, Terpenes and Phenylpropanoids

Isolation of Eugenol from Cloves

Essay

Stereochemical Theory of Odor

Spearmint and Caraway Oil: (+)- and (-)- Carvones

Essay

The Chemistry of Vision

Isolation of Chlorophyll and Carotenoid Pigments from Spinach

Essay: Ethanol and Fermentation Chemistry

Ethanol from Sucrose

Introduction to Molecular Modeling

Essay: Molecular Modeling and Molecular Mechanics

An Introduction to Molecular Modeling

The Conformations of n-Butane: Local Minima

Cyclohexane Chair and Boat Conformations

Substituted Cyclohexane Rings (Critical Thinking Exercise)

cis- and trans-2-Butene

Essay: Computational Chemistry - Ab initio and Semiempirical Methods

Computational Chemistry

Heats of Formation: Isomerism, Tautomerism, and Regioselectivity

Heats of Reactions: SN1 Reaction Rates

Density-Electrostatic Potential

Maps: Acidities of Carboxylic Acids

Density -Electrostatic Potential Maps: Carbocations

Density -LUMO Maps: Reactivities of Carbonyl Groups

Preparations and Reactions of Organic Compounds

Reactivities of Some Alkyl Halides

Nucleophilic Substitution Reactions: Competing Nucleophiles

Competing Nucleophiles with 1-Butanol or 2-Butanol

Competing Nucleophiles with 2-Methyl-2-Propanol

Analysis

Synthesis of n-Butyl Bromide and t-Pentyl Chloride

n-Butyl Bromide

t-Pentyl Chloride

4-Methylcyclohexene Essay

Fats and Oils

Methyl Stearate from Methyl Oleate

Essay: Petroleum and Fossil Fuels

Gas Chromatographic Analysis of Gasolines

Essay: Biofuels

Biodiesel

Biodiesel from Coconut Oil

Biodiesel from Other Oils

Analysis of Biodiesel

Ethanol from Corn

Essay: Green Chemistry

Chiral Reduction of Ethyl Acetoacetate; Optical Purity Determination

Chiral Reduction of Ethyl Acetoacetate

NMR Determination of the Optical Purity of Ethyl (S)-3-Hydroxybutanoate

Nitration of Aromatic Compounds Using a Recyclable Catalyst

Reduction of Ketones Using Carrots as Biological Reducing Agents

Resolution of (+/-)-alpha-Phenylethylamine and Determination of Optical Purity

Resolution of (+/-)-alpha-Phenylethylamine

Determination of Optical Purity Using NMR and a Chiral Resolving Agent

An Oxidation-Reduction Scheme: Borneol, Camphor, Isoborneol

Multistep Reaction Sequences: The Conversion of Benzaldehyde to Benzilic Acid

Preparation of Benzoin by Thiamine Catalysis

Preparation of Benzil

Preparation of Benzilic Acid

Triphenylmethanol and Benzoic Acid

Triphenylmethanol

Benzoic Acid

Aqueous-Based Organozinc Reactions

Sonogashira Coupling of Iodosubstituted Aromatic Compounds with Alkynes Using a Palladium Catalyst

Grubbs Catalyzed Metathesis of Eugenol with 1,4-Butenediol to Prepare a Natural Product